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Articles by Matthew
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The Storefront Transition: Catalog to Journey
The Storefront Transition: Catalog to Journey
E-commerce sites have always functioned as online catalogs. Consumers search, scroll, and click through facets, hoping…
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The Case for an AI-First ESP: The Next Billion-Dollar OpportunityMar 19, 2026
The Case for an AI-First ESP: The Next Billion-Dollar Opportunity
The Email Service Provider (“ESP”) market has generated more billion-dollar exits than any other category in commerce…
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The End of the Middleman Economy: How AI Agents Will Disrupt High-Take-Rate PlatformsFeb 2, 2026
The End of the Middleman Economy: How AI Agents Will Disrupt High-Take-Rate Platforms
For the past decade, we've watched platform intermediaries build seemingly unassailable moats. DoorDash, Instacart…
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Is "ChatGPT Prime" the Future of Loyalty Programs in the Age of Agentic Shopping?Oct 8, 2025
Is "ChatGPT Prime" the Future of Loyalty Programs in the Age of Agentic Shopping?
AI agents aren’t just changing how we search. They’re beginning to change how we shop.
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Who Owns Shopping Data in the Age of AI?Aug 8, 2025
Who Owns Shopping Data in the Age of AI?
AI is changing how we shop online and sparking a tug-of-war over who controls the data that powers those experiences…
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Why “Shopify for B2B” Might Finally Work—Thanks to AIJul 1, 2025
Why “Shopify for B2B” Might Finally Work—Thanks to AI
For years, entrepreneurs and investors have been chasing the dream of a “Shopify for B2B”—a seamless, digital-first…
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Agentic Commerce is HereMay 2, 2025
Agentic Commerce is Here
AI is beginning to change the way we shop online. This week, OpenAI announced “ChatGPT Shopping,” a new feature that…
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The Evolution of Online Travel Agencies and the Opportunity for “Headless OTAs”Feb 12, 2025
The Evolution of Online Travel Agencies and the Opportunity for “Headless OTAs”
The Online Travel Agency (OTA) market has undergone significant transformations since its inception, evolving through…
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Activity
4K followers
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Matthew Nichols shared thisGreat new product from Lioran Pinchevski and the whole Finaloop team. When I ran a brand, we spent so much time and effort building tools and hiring people to do a fraction of what Margins can do. I wish this product was around 10 years ago!
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Matthew Nichols shared thisIt's been a while since we've seen a fundamentally new ecommerce platform. We think the time is now. As consumers become accustomed to LLM-based journeys, they will expect those journey's to continue as they migrate to ecommerce sites. This will require an entirely new approach. One that embraces journeys over static catalogs, and continues the conversation from LLMs and other AI-native discovery tools.The Storefront Transition: Catalog to JourneyThe Storefront Transition: Catalog to JourneyMatthew Nichols
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Matthew Nichols shared thisIt was great to see so many of our LPs, portfolio company CEOs, and friends at our Commerce Summit last week. We covered a lot of ground - from Stablecoins to Agentic Commerce, and everything in between.
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Matthew Nichols shared thisCongrats Scot Wingo and the ReFiBuy.ai team. Thanks for including us in your journey at both the pre-seed and seed rounds. Agentic Commerce is already changing retail, and I couldn't think of a better team to go after this opportunity!Matthew Nichols shared thisToday, we’re excited to announce $13.6M in oversubscribed Seed funding. The round was led by NewRoad Capital Partners, with participation from Ridge Ventures, Silicon Road Ventures, Incubate Fund, Vela Partners, G20 Ventures, Commerce Ventures, Knoll Ventures, and retail industry angel investors. The next platform shift in commerce is here. AI shopping agents are becoming the new interface consumers use to research, find, and buy products. Most product catalogs, however, were built for human browsing, marketplace feeds, and keyword-driven discovery, not for the way agents evaluate and recommend products. That shift is creating a new operating discipline for commerce teams: Agentic Commerce Optimization (ACO). We defined ACO and built the platform to operationalize it, giving brands and retailers the infrastructure they need to prepare their catalogs for AI-powered shopping. This funding will help us scale the platform, accelerate go-to-market, and support more brands and retailers as they compete in the agentic commerce era. Thank you to our customers, investors, partners, advisors, and team for helping us build the commerce intelligence layer for what comes next. We’re just getting started. Read the full announcement: https://lnkd.in/e7utAgxX
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Matthew Nichols shared thisWe are excited to be on the journey together with Wiley Jones, Arnav Mishra, and the entire DOSS team. We've had a long-running thesis around the need for a modern ERP and were incredibly impressed by what the Doss team has built. As a former retail exec who nearly made the mistake of doing a full Netsuite implementation, I know the pain of needing an operational system, but not wanting to adapt my business to fit a piece of outdated software.Matthew Nichols shared thisAfter 3.5 years of building and absolutely RIPPING Celsius… We’re announcing that DOSS has raised a $55M Series B, co-led by Madrona and Premji Invest, with Greyhound Capital, Commerce Ventures, Pathlight Ventures, and Intuit Ventures as new investors, and continued investment from Theory Ventures, General Catalyst, Contrary, and Mintaka VC. Before starting DOSS I worked on numerous hardware products. Honestly my opinion today is pretty much unchanged: it’s a miracle that any get built at all. I saw firsthand how the physical world runs on systems that were designed by people who’d never use them. Teams would adapt their entire business strategy to fit into the shape of off-the-shelf applications and would spend 4-10x more on consulting time than on the software itself. Worst of all - they’d wait YEARS for implementations to complete which ultimately wouldn’t reflect how the business actually functioned by the time it was live. That's the problem we're solving. DOSS is the Operations Cloud built for the Real World. We sit around your general ledger and model how your business actually runs. Procurement, inventory, orders, finance, all connected, all in real time. We're already seeing it work. Teams with individual people saving 20+ hours a week (that’s half of their time!). Companies growing 3x in a year without adding any headcount to operations. With Operations Cloud, teams are putting up Hall of Fame stats and we’re. just. getting. started. HUGE thank you to our customers, our new investors, our long-time advisors, and most of all the DOSS TEAM!!!! We're building something that can stand the test of time (no small feat in enterprise software). Enabling platform shifts like this happen roughly once a generation and as Jeremy Irons says in Margin Call, “Don’t you understand? THIS IS IT!” ONWARD! There’s work to be done.
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Matthew Nichols shared thisCongrats to Josh Payne and the Coframe team for winning the judges' choice award in the startup competition at Shoptalk. As part of our partnership with Shoptalk, we have awarded Coframe a $100k investment from Commerce Ventures. Excited to have Josh and the team join the Commerce Ventures family! It was great to evaluate so many great companies alongside my co-judges Deborah Weinswig 韋葆蘭, Kamanasish Kundu, and Brent Murri.
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Matthew Nichols shared thisThe opportunity to build an AI-native email platform is one of the largest opportunities sitting in plain sight. It has been the category in commerce infrastructure that has produced the most $1Bn+ exits, and yet everyone seems to think there won't be a new killer email platform. I think they are wrong...The Case for an AI-First ESP: The Next Billion-Dollar OpportunityThe Case for an AI-First ESP: The Next Billion-Dollar OpportunityMatthew Nichols
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Matthew Nichols shared thisSo proud of John Andrews , Vivek and the full Cimulate AI team. We were fortunate enough to be investors and appreciate all of the hard work to get to this outcome.Matthew Nichols shared thisToday is a very big day for the team at Cimulate. We announced that we signed a definitive agreement to be acquired by Salesforce. Moments like this only happen when the right idea meets the right technology, team, and market timing. Over the past few years generative AI has fundamentally changed the way people – and now agents – buy. We were fortunate to be building for that future just as the market was ready for it. Salesforce has been making significant investments in Agentforce Commerce, and their acquisition of Cimulate is a testament to their deep commitment to the future of agentic commerce. We couldn’t imagine a better partner to help scale Cimulate, and my co-founder Vivek and I have felt great alignment since the very first conversation. As one of our investors said, if the stars align, you don’t fight the fortuitous gravitational pull. This is only the beginning! To our team and customers: Get excited. We are going to be able to build faster and deliver even greater impact than we could have alone. Read the full announcement in the Salesforce Newsroom: https://lnkd.in/enb-H6rg Read more from me on our website: https://lnkd.in/evY4jNasBuilding the Future of Commerce Together with Salesforce - Cimulate AIBuilding the Future of Commerce Together with Salesforce - Cimulate AI
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Matthew Nichols shared thisI write here about why high-take rate intermediaries may be at risk as Agentic Commerce gains momentum.The End of the Middleman Economy: How AI Agents Will Disrupt High-Take-Rate PlatformsThe End of the Middleman Economy: How AI Agents Will Disrupt High-Take-Rate PlatformsMatthew Nichols
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Matthew Nichols liked thisMatthew Nichols liked thisI never wanted the Patagonia vest, but damn I always thought venture capital was cool. When I was 26, the feeling was decidedly not mutual. I was rejected by a soul-crushing 35 VC funds. I decided to get my yah yahs out playing drums in two very politically incorrect bands before starting to grind as an entrepreneur. I learned how to hire, raise capital, hit payroll, acquire companies, suffer panic attacks, and mercifully engineer two exits. Twenty years building companies in the arena taught me how to speak founder. I could help people make sense of the 0 to 1. And I could empathize with the regular kicks to the nuts that is entrepreneurialism. So, in 2022 I gave myself the VC job no one else would. mu ventures is now 46 companies strong. We also built the Rec Room for deal sharing, Tap Night for meeting top-tier founders, and the Mu-niversal Get Down, our annual bacchanal. None of it feels like work. We’re now 5 years in, and I’m keepin’ the job baby! Today we closed Mu Ventures II, a $15.5M pre-seed and seed stage fund anchored by AngelList Asset Management, their quantitative fund of funds. These guys are brilliant, and their model for predicting future fund performance chose us. Their team reached out because our performance ranked top 3% of the hundreds of funds on their platform. We're incredibly thankful for their support, and the support of Dynamism Capital and our other 63 LPs. Now the most important part…. Founders - if you want a super competitive, fun-loving maniac that will never stop hustling for you, keep reading. We will evaluate you on the merits, not on your cap table. We don’t borrow conviction from anyone. We’ll treat you like a person, and not a return profile, because we kind of need to like you. Life is too short to back assholes. We're focused on Vertical AI, with plenty of marketplaces, CPG, and commerce infra in the portfolio. But mostly, we’re founder-obsessed, not category-constrained. Our sweet spot is $200-600k checks into pre-seed companies raising under $10m post and seed companies raising under $20m post. If you're one of the beautifully insane maniacs ripping friction out of something big, and you naturally attract talent, customers, and capital, come find me!
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Matthew Nichols liked thisMatthew Nichols liked thisAfter nearly 11 incredible years, I’ve wrapped up my journey at Toast. It’s hard to capture what makes Toast such a special place, but three things stand out: First, an unwavering commitment to customers. Every decision starts with helping restaurants + retailers succeed, and that focus has always been at the heart of the company. Second, the people. I’ve never worked with a team that cared more deeply or brought more energy to solving hard problems - all while having a little fun along the way. And finally, the opportunity to be part of an exponential chapter of growth. I joined Toast in 2015 when it was still in its early days and had the privilege of helping build the company into what it is today. Seeing that journey unfold has been an extraordinary experience. Aman Narang, Steve Fredette and Jonathan Grimm - thank you for the opportunity. To Michel Rbeiz, Nick DeLeonardis and Tim Barash - thank you for your support. To Elena Gomez - thank you for the mentorship. What I’ll miss most are people - the Toasters, customers and partners - I had the privilege of working and growing alongside. Thank you to everyone who made the past 11 years so memorable, I hope our paths cross again. To the Fintech and Payments teams I had the honor of leading - thanks for having me. Watching so many of you grow into exceptional operators + leaders and being part of that journey has been immensely rewarding. You are the reason this was a difficult decision and I will miss everyone. As for what’s next, I’m taking a break to spend time with my family, especially my two young daughters. If you asked my girls what I did at Toast, they’d tell you, “bossing” - a description I find equal parts hilarious and horrifying. For now, this next chapter is all about them and I’m sure they will waste no time reminding me who’s really in charge. I was lucky enough to have them help me close it out right on Toast’s ‘Crouton Day’ earlier this month, here is a snap from that day along with a few other favorites -
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Matthew Nichols liked thisMatthew Nichols liked thisOur 2nd annual Innovators Showcase at NRF Retail's Big Show Europe is shaping up to be a “can’t miss event!” This year’s exhibitors are bringing groundbreaking AI technologies addressing top retailer priorities – from customer retention and online conversion, to in-store engagement and product discovery, inventory management, last-mile delivery and much more. Want to be part of this exclusive retail-tech showcase? Applications close July 10th – and spots are filling up fast. Secure yours today by applying here: https://lnkd.in/dRZmiVwM Thank you to the NRF Advisory Committee for help identifying top technologies: Scott Friend, Dave Finnegan, Karla Martin, Miguel Bagulho, Susan Akbarpour, Tessa Flippin, Debra Langley, Arpon Ray, Matthew Nichols, Smriti Jayaraman Kekre, Bill Purcell, Richard (Rickie) Koo, Leo Nagdas, David Grant, Marigay McKee, Sucharita Kodali, Saranathan Govindarajan, Jean-Michel Kientz, Kathy Gromotka, Claire Chang,Logan Langberg, Vincent Diallo, Peter Burggraaff OLY, Janie Yu, Alicia Teo, Greg Merrill, Josh Jewett, Ignacio Miranda, Oren Paran, David Matthews, Sid Mookerji, Andrew Stott, Jackie T., Richard Kestenbaum, Liam Buswell, Ingrid Maes, Ram Rampalli, Seth Webb. #NRF2026 #NRFEurope #InnovatorsShowcase #RetailTechnology #Startups #ConsumerTech #AgenticCommerce #AI
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Daniel Dart
Rock Yard Ventures • 10K followers
🚨NEW EPISODE: Recorded live at FUTURE TITANS 2026 - Jeff Perry of Carta sat down with the iconic Seth Levine, co-founder of Foundry. Seth has been in venture for 25 years, built Foundry from scratch as an emerging manager himself, and has backed about 50 emerging manager funds through his fund of funds. He has genuinely seen every side of this table. They went deep on building Foundry, why VCs are in the influence business, not the decision business, and why the concentration problem in venture is not only bad for LPs, but also for the innovation ecosystem overall. And why Seth's new book, Capital Evolution, is so important for the future of America. 🎧 Links to listen... Apple: https://lnkd.in/ehQUQ2EM Spotify: https://lnkd.in/eU4FExpg
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Earnest Sweat
Stresswood • 18K followers
Venture has always been a power law. What’s changing is how tightly LPs are underwriting to it. In our conversation with David Clark, one point stood out: If a small group of managers consistently capture the outliers… That’s where capital concentrates. Which makes the middle a harder category to underwrite. Not because those firms are underperforming, but because the case for why this manager gets you to those outcomes is less clear. It’s not about returns in isolation. It’s about conviction. To earn real conviction from LPs today, what do you think a middle firm needs to show? 👇 Link in the comments.
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Jeffrey Seah
MSW Ventures • 7K followers
🥾 #bootstrapping as a mindset should be ephemeral, one that requires a deliberate transition away from as a business enters sustained growth Appointing an established auditor is often regarded as a luxury and not part of bootstrapping Audits discipline a business - to be methodical, thorough and deliberate - traits that acquirers often seek in due diligence After all, "What gets inspected, gets respected," Anon We will share the traits of venture businesses sought and respected by MNC acquirers, join us if your business is out of the #bootstrapping mindset #fulfillingpotential #hepmil #oobmil
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Harvrinder Athwal
XSS Capital Ltd. • 28K followers
Can fundraising teams detect a stalled process before silence becomes the strategy? The forwardable lesson is that long sales cycles need an early-warning layer, not simply more activity at the top of the funnel. The system is designed to recommend action, not merely record that progress slowed. The Long Cycle RAISE combines mandate scoring, allocation signals, trigger detection and pipeline intelligence to surface issues earlier. The Warning Layer The workflow can track investor stage, relationship activity, soft commitments, hard commitments and risks around the target process. The Waiting Problem The company is addressing a process that managers already understand and repeatedly need to solve. RAISE is raising capital and looking for investors. See company website https://raiseplatform.eu and then DM me for more info. Is faster feedback more valuable than faster outreach in institutional fundraising?
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Tom Lazay
Companyon Ventures • 5K followers
An emerging VC manager's fundraising lessons... the first two funds are a grind. Now, we’re on our third fund, it feels like we’re almost over the hump, but fundraising never gets easy for most of us. I want to congratulate the emerging VC firms presenting at this year’s RAISE Global conference. As former RAISE presenters, and (soon-to-graduate) emerging managers, we thought we’d share this LP Translator, a lighthearted guide to decoding what LPs really mean during the fundraising process. Fellow GPs, which ones did I miss? 👇 The LP Translator 📣 "Let’s stay in touch.” Translation: We’re not interested. “We want to see your track record develop.” Translation: Either we don't believe in your strategy, or we’re focused on managers with more buzz. “We’re not allocating to new managers right now.” Translation: We’re not allocating to you right now. "Show us your deals so we can get to know you.” Translation: We’d like free co-invests if you get something hot. “We need to see more DPI before we commit.” Translation: We don’t really understand VC, but we’re pretending to. “We’re fully allocated for this year; check in early next year.” Translation: Next year we’ll still be fully allocated (just not to you). “Call us before final close.” Translation: I’m too polite to say no at this time, so I’m kicking the can down the road. “Your fund is too small.” Translation: Okay, that one might actually be true (for some LPs). “We went through your data room and want to meet face-to-face.” Translation: We’re genuinely interested, keep going! “Can you send us your LPA for signature?” Translation: Let’s go! 🚀 -------------------------- Fundraising is a long game, longer than we ever expected. We're now seeing how LP relationships are built across several funds, not several months. If they’re investing time to learn about you and your strategy, that’s your best signal of real interest. #emergingmanager #venturecapital #LP #RAISEGLOBAL
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Henry D. Wolfe
DaVega & Wolfe Industries… • 2K followers
Randian Capital a Shareholder of Snap Inc. Publishes Open Letter to Board and Management, and Announces Snap Investor Town Hall On 4/6 at 7PM EST live on X "Snap’s governance structure—in which public shareholders have effectively no voice—is among the worst we have encountered across public markets. The Company’s governance and capital allocation practices together represent a textbook case of how to prevent the formation of a durable, long-term shareholder base. "Snap’s stock currently trades near an all-time low, having declined over 80% since the IPO (based on IPO close price to 3/30 closing price). Shareholders—many of them retail investors who believed in the Company’s vision—have endured years of value erosion with no credible path to recovery in sight. If the Board does not act with urgency, we believe Snap faces a real risk of permanent impairment and irreversible decline." #governancearbitrage #valuecreation #corporategoverance https://lnkd.in/gJRcfuVG
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